Water → N-(2-Nitro-4-((4-phenylpiperazin-1-yl)methyl)phenylmethyl)acetamide

HRID 1282069Notes

Reaction equation

HRID 1282069 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=1.[CH:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[N+:14]([C:5]1[CH:4]=[C:3]([CH2:2][N:26]2[CH2:27][CH2:28][N:23]([C:20]3[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=3)[CH2:24][CH2:25]2)[CH:8]=[CH:7][C:6]=1[CH2:9][NH:10][C:11](=[O:13])[CH3:12])([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 18423048N-(4-chloromethyl-2-nitrophenylmethyl)acetamide

Product 1

HCID 18423156N-(2-Nitro-4-((4-phenylpiperazin-1-yl)methyl)phenylmethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-chloromethyl-2-nitrophenylmethyl)acetamide (1.4 g), phenylpiperazine (0.8 ml) and potassium carbonate (0.6 g) in dimethylformamide (20 ml) was stirred at 60° C. for 4 hr. The reaction mixture was poured into water (150 ml) and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a pale-yellow solid. The obtained pale-yellow solid was crystallized from ethyl acetate to give the title compound (1.3 g) as pale-yellow white crystals, m.p.=135-136° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customto give a pale-yellow solid
  6. customThe obtained pale-yellow solid was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-2e80df1a263b431a8db76cf703108157
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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